Aniline → N,N-Dioctadecylaniline

HRID 414442Notes

Reaction equation

HRID 414442 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>[I-].[Na+].C(O)CCC>[CH2:14]([N:1]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 6115AnilineHCID 82181-BromooctadecaneHCID 11430Potassium Carbonate

Product 1

HCID 4106142N,N-DioctadecylanilineYield 54%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 2631-ButanolSolvent

Procedure

A mixture of freshly distilled aniline (93 g, 1 mol), potassium carbonate (210 g, 1.5 mol), octadecyl bromide (840 g, 2.5 mol), sodium iodide (7.5 g, 0.05 mol), and 1 liter of butanol was heated at reflux for 72 hours under nitrogen with vigorous stirring. The hot solution was filtered and the filtrate was evaporated under reduced pressure. The residue was recrystallized from absolute ethanol to yield 322 g (54%) of off-white crystals mp 110°-111° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 72 hours under nitrogen with vigorous stirring
  3. filtrationThe hot solution was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-dfbfdcc94c0e4209b6782e112605a928
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

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